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Showing Compound Hypoxanthine (FDB003949)

Record Information
Version1.0
Creation date2010-04-08 22:06:01 UTC
Update date2020-09-17 15:38:22 UTC
Primary IDFDB003949
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameHypoxanthine
DescriptionHypoxanthine, also known as purine-6-ol or Hyp, belongs to the class of organic compounds known as hypoxanthines. Hypoxanthines are compounds containing the purine derivative 1H-purin-6(9H)-one. Purine is a bicyclic aromatic compound made up of a pyrimidine ring fused to an imidazole ring. A purine nucleobase that consists of purine bearing an oxo substituent at position 6. Hypoxanthine is a moderately basic compound (based on its pKa). Hypoxanthine exists in all living species, ranging from bacteria to humans. Within humans, hypoxanthine participates in a number of enzymatic reactions. In particular, hypoxanthine and ribose 1-phosphate can be biosynthesized from inosine; which is mediated by the enzyme purine nucleoside phosphorylase. In addition, hypoxanthine and phosphoribosyl pyrophosphate can be biosynthesized from inosinic acid; which is catalyzed by the enzyme hypoxanthine-guanine phosphoribosyltransferase. In humans, hypoxanthine is involved in purine metabolism. Outside of the human body, Hypoxanthine is found, on average, in the highest concentration within beers and milk (cow). Hypoxanthine has also been detected, but not quantified in, several different foods, such as pigeon pea, green vegetables, lovages, gram beans, and arrowhead. This could make hypoxanthine a potential biomarker for the consumption of these foods. Hypoxanthine is a potentially toxic compound.
CAS Number68-94-0
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
6(1H)-PurinoneChEBI
6-OxopurineChEBI
9H-Purin-6(1H)-oneChEBI
HypChEBI
Purin-6(1H)-oneChEBI
Purine-6-olChEBI
1,7-Dihydro-6H-purin-6-oneHMDB
1,7-Dihydro-6H-purine-6-oneHMDB
1H,7H-HypoxanthineHMDB
3H-Purin-6-olHMDB
4-Hydroxy-1H-purineHMDB
6-Hydroxy-1H-purineHMDB
6-HydroxypurineHMDB
7H-Purin-6-olHMDB
9H-Purin-6-olHMDB
Hypoxanthine enolHMDB
Purin-6(3H)-oneHMDB
Purin-6-olHMDB
SarcineHMDB
SarkinHMDB
SarkineHMDB
1,7-dihydro-6H-Purin-6-oneHMDB
1,9-Dihydro-purin-6-onebiospider
6H-Purin-6-one, 1,7-dihydro-biospider
6H-Purin-6-one, 1,9-dihydro-biospider
Hypoxanthinebiospider
Imidazo[5,4-d]pyrimidine, 6-hydroxy-biospider
Predicted Properties
PropertyValueSource
Water Solubility13 g/LALOGPS
logP-0.55ALOGPS
logP-0.048ChemAxon
logS-1ALOGPS
pKa (Strongest Acidic)8.72ChemAxon
pKa (Strongest Basic)1.73ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.69 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity35.5 m³·mol⁻¹ChemAxon
Polarizability11.82 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC5H4N4O
IUPAC name7H-purin-6-ol
InChI IdentifierInChI=1S/C5H4N4O/c10-5-3-4(7-1-6-3)8-2-9-5/h1-2H,(H2,6,7,8,9,10)
InChI KeyFDGQSTZJBFJUBT-UHFFFAOYSA-N
Isomeric SMILESOC1=NC=NC2=C1NC=N2
Average Molecular Weight136.1115
Monoisotopic Molecular Weight136.03851077
Classification
Description Belongs to the class of organic compounds known as hypoxanthines. Hypoxanthines are compounds containing the purine derivative 1H-purin-6(9H)-one. Purine is a bicyclic aromatic compound made up of a pyrimidine ring fused to an imidazole ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassImidazopyrimidines
Sub ClassPurines and purine derivatives
Direct ParentHypoxanthines
Alternative Parents
Substituents
  • 6-oxopurine
  • Hypoxanthine
  • Pyrimidone
  • Pyrimidine
  • Azole
  • Imidazole
  • Vinylogous amide
  • Heteroaromatic compound
  • Azacycle
  • Organic oxide
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNeedlesCCD
Mass CompositionC 44.12%; H 2.96%; N 41.16%; O 11.75%CCD
Melting PointMp 360°CCD
Boiling PointNot Available
Experimental Water Solubility0.7 mg/mL at 23 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP-1.11HANSCH,C ET AL. (1995)
Experimental pKap Ka11.91 ( 20° ) p Ka28.96 ( 20° ) p Ka312.18 ( 20° )CCD
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-000i-8900000000-ebf57ea530a2d4e31ffa2014-09-20View Spectrum
GC-MSHypoxanthine, 2 TMS, GC-MS Spectrumsplash10-0159-3970000000-0d844fae4a1ffe158823Spectrum
GC-MSHypoxanthine, non-derivatized, GC-MS Spectrumsplash10-014i-1790000000-ae93bf8bf07b30b65e1aSpectrum
GC-MSHypoxanthine, 2 TMS, GC-MS Spectrumsplash10-00di-9340000000-1184c503fb61344c4853Spectrum
GC-MSHypoxanthine, 2 TMS, GC-MS Spectrumsplash10-014i-3590000000-a419976950afe7934cbcSpectrum
GC-MSHypoxanthine, non-derivatized, GC-MS Spectrumsplash10-000i-9800000000-9c266d6963658e9d2cf1Spectrum
GC-MSHypoxanthine, non-derivatized, GC-MS Spectrumsplash10-0159-3970000000-0d844fae4a1ffe158823Spectrum
GC-MSHypoxanthine, non-derivatized, GC-MS Spectrumsplash10-014i-1790000000-ae93bf8bf07b30b65e1aSpectrum
GC-MSHypoxanthine, non-derivatized, GC-MS Spectrumsplash10-00di-9340000000-1184c503fb61344c4853Spectrum
GC-MSHypoxanthine, non-derivatized, GC-MS Spectrumsplash10-014i-3590000000-a419976950afe7934cbcSpectrum
GC-MSHypoxanthine, non-derivatized, GC-MS Spectrumsplash10-014i-2890000000-3be4d08be45781881bc1Spectrum
GC-MSHypoxanthine, non-derivatized, GC-MS Spectrumsplash10-014i-1590000000-bb6f003bfa7bd04628a1Spectrum
Predicted GC-MSHypoxanthine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a5i-8900000000-e20eb5d939a2c406a6e2Spectrum
Predicted GC-MSHypoxanthine, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0613-5900000000-be0624b928ba71cc797dSpectrum
Predicted GC-MSHypoxanthine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSHypoxanthine, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSHypoxanthine, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSHypoxanthine, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000i-0900000000-2b36c20acd9973b317f52012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0api-9800000000-fb4e3cccb7d27d119feb2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0aor-9200000000-33c2f9eedf9a878530be2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-000i-9800000000-9c266d6963658e9d2cf12012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-0910000000-4da64abddc3ac8ab573a2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-014i-1900000000-859f61101b12be0b29782012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-014i-1900000000-f5d899e7988568d5bcab2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-0900000000-e19e6d04568d3560eb4a2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-0910000000-8def0d2ec821528267632012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-014i-2900000000-a8361951a2f702a217c72012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-0900000000-3f653a7c81b328e46cb52012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-014i-0080290000-be98ce43421dbf9007fa2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-000i-0930030000-56ea204dcb077bc174c22012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0006-9000000000-4c2d1980f9e5e4b720a52012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-000i-0900000000-26b3c93bc9dea5a880322012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-000i-1900000000-c367cd4c23aea0f74ecb2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-000l-8900000000-91e35cdcc11d357119f02012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0006-9100000000-4fb8f4ee2d35aa8746172012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-014l-9000000000-7934b3037f39d69fc40a2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-014i-9000000000-ad93e267446292bf247b2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-014i-9000000000-4b8f9e13ed7adf0888c22012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-014i-9000000000-f295755f591e27bb9f072012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-014i-9000000000-aee48a44f42a4b7678442012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-014i-9000000000-f5ebd92e86cf00f28cf12012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-014i-9000000000-9a1ad1aa2d8fb621b6082012-08-31View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 22.53 MHz, DMSO-d6, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
2D NMR[1H, 1H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)Spectrum
ChemSpider ID768
ChEMBL IDCHEMBL1427
KEGG Compound IDC00262
Pubchem Compound ID790
Pubchem Substance IDNot Available
ChEBI ID17368
Phenol-Explorer IDNot Available
DrugBank IDDB04076
HMDB IDHMDB00157
CRC / DFC (Dictionary of Food Compounds) IDBVX59-I:BVX59-I
EAFUS IDNot Available
Dr. Duke IDHYPOXANTHINE|HYPOXANTHIN
BIGG ID34434
KNApSAcK IDNot Available
HET IDHPA
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDHypoxanthine
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Purine nucleoside phosphorylasePNPP00491
Equilibrative nucleoside transporter 2SLC29A2Q14542
Pathways
NameSMPDB LinkKEGG Link
Purine MetabolismSMP00050 map00230
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).